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US12091546B2 - Condensation curable compositions - Google Patents

Condensation curable compositions Download PDF

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US12091546B2
US12091546B2 US17/043,190 US201917043190A US12091546B2 US 12091546 B2 US12091546 B2 US 12091546B2 US 201917043190 A US201917043190 A US 201917043190A US 12091546 B2 US12091546 B2 US 12091546B2
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silicone elastomer
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US20210147682A1 (en
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Tatiana Dimitrova
Anne-Marie Van Stiphoudt
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Dow Silicones Corp
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Dow Silicones Corp
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • C08K5/57—Organo-tin compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/08—Oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/10—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/006—Additives being defined by their surface area

Definitions

  • This disclosure concerns a condensation cure organosiloxane composition that may be used as an electrically insulating sealant and/or adhesive.
  • Condensation curable organosiloxane compositions which cure to elastomeric solids, are well known.
  • such compositions are obtained by mixing a polydiorganosiloxane having reactive terminal groups, e.g. hydroxy groups or hydrolysable groups, with e.g. a silane cross-linking agent which is reactive with the polydiorganosiloxane, for example an acetoxy silane, an oximosilane, an aminosilane or an alkoxysilane in the presence of a suitable catalyst.
  • Such compositions typically contain reinforcing fillers such as silica and/or calcium carbonate to enhance their physical properties.
  • compositions can be commercialized as one-part or two-part compositions.
  • the former one-part compositions
  • cure in contact with atmospheric moisture.
  • the latter two-part compositions
  • curing agent shall be used to denote the part containing the catalyst, the cross-linker and optionally other ingredients, but excluding the polydiorganosiloxane having reactive terminal groups.
  • Sealants, encapsulants and adhesives are increasingly being used to replace mechanical fixtures and the like in a wide variety of situations and applications often allowing for cheaper and faster production processes in the manufacture of articles.
  • Increasingly at least some of the parts of such articles contain electrical circuitry resulting in the need for suitable sealants to adhere and/or seal-assembled parts of such articles as well as to function as insulators.
  • Typical examples where it would be beneficial to use an electrically insulating silicone sealant or adhesive include, but are not limited to, sealants and adhesives in photovoltaic applications where they are required to develop permanent seals and/or adhesion between parts and adjacent materials and/or parts such as glass, metal and plastic substrates.
  • the insulative character of the material must be preserved over time, e.g.
  • sealant/adhesive compositions have been proposed and silicone-based materials are some of the most favoured.
  • Hydrosilylation cure silicone compositions are not generally preferred because they are poor adherents, whilst condensation cure systems can be problematic because they are in some instances not sufficiently good insulators.
  • volume resistivity (ohms ⁇ cm ( ⁇ cm)) is the measurement of the “bulk” resistivity of a material i.e. it discloses the inherent resistance of a tested specimen regardless of its shape or size.
  • volume resistivity is the resistance to leakage current through the body of an insulating material.
  • Surface resistivity is the resistance to leakage current along the surface of an insulating material.
  • silicone elastomer composition comprising:
  • a silicone elastomer obtained by curing a composition comprising:
  • the polydiorganosiloxane having at least two —OH or hydrolysable groups per molecule (a) may be depicted by the following Formula (1): X 3-n R n Si—(Z) d —(O) q —(R 1 y SiO (4-y)/2 ) z —(SiR 1 2 —Z) d —Si—R n X 3-n (1)
  • n 0, 1, 2 or 3
  • z is an integer from 200 to 5000 inclusive
  • y is 0, 1 or 2, alternatively is 2.
  • X is a hydroxyl group or alkoxy group or any condensable or any hydrolyzable group
  • R is individually selected from the group consisting of aliphatic groups such as alkyl, substituted alkyl, e g aminoalkyl, polyaminoalkyl, epoxyalkyl, and alkenyl groups or aromatic aryl groups
  • R′ is individually selected from the group consisting of X, aliphatic alkyl groups, aliphatic alkenyl groups and aromatic groups.
  • the polydiorganosiloxane (a) can be a single siloxane represented by Formula (1) or it can be mixtures of siloxanes represented by the aforesaid formula or solvent/polymer mixtures.
  • polymer mixture is meant to include any of these types of polymers or mixtures of polymers.
  • Each X group may be the same or different and can be a hydroxyl group and any condensable or hydrolyzable group.
  • the term “hydrolyzable group” means any group attached to the silicon which is hydrolyzed by water at room temperature.
  • the hydrolyzable group X includes groups of the Formula —OT, where T is any hydrocarbon or halogenated hydrocarbon group, such as methyl, ethyl, isopropyl, octadecyl, allyl, hexenyl, cyclohexyl, phenyl, benzyl, beta-phenylethyl; any hydrocarbon ether radical, such as 2-methoxyethyl, 2-ethoxyisopropyl, 2-butoxyisobutyl, p-methoxyphenyl or —(CH 2 CH 2 O) 2 CH 3 ; or any N,N-amino radical, such as dimethylamino, diethylamino, ethyl
  • the most preferred X groups of the invention are hydroxyl groups or alkoxy groups.
  • Illustrative alkoxy groups are methoxy, ethoxy, propoxy, butoxy, isobutoxy, pentoxy, hexoxy and 2-ethylhexoxy; dialkoxy radicals, such as methoxymethoxy or ethoxymethoxy and alkoxyaryloxy, such as ethoxyphenoxy.
  • the most preferred alkoxy groups are methoxy or ethoxy.
  • R is individually selected from the group consisting of aliphatic groups, such as alkyl groups, substituted alkyl groups e.g. aminoalkyl, polyaminoalkyl, epoxyalkyl, groups and alkenyl groups and aromatic aryl groups. Most preferred are the methyl, ethyl, octyl, vinyl, allyl and phenyl groups.
  • R 1 is individually selected from the group consisting of X groups or aliphatic alkyl groups, aliphatic alkenyl groups and aromatic groups as described above.
  • R 1 groups are selected from methyl, ethyl, octyl, trifluoropropyl, vinyl and phenyl groups. It is possible that some R 1 groups may be siloxane branches off the polymer backbone which may have terminal groups as hereinbefore described.
  • Z is independently a saturated, bi-valent aliphatic radical of the type of C w H 2w where w is 2 or more, alternatively w is from 2 to 10.
  • Polydiorganosiloxane (a) may be present in the form of a single polymer, or as a blend of polydiorganosiloxanes (a) having different degrees of values of z in formula (1) above.
  • the Degree of Polymerization (DP) in a macromolecule or polymer or oligomer molecule of silicone, in this case polydiorganosiloxane (a) is usually defined as the number of monomeric units therein.
  • Synthetic polymers invariably consist of a mixture of macromolecular species with different degrees of polymerization and therefore of different molecular weights.
  • M n and Mw values of silicone can be determined by Gel permeation chromatography (GPC) with precision of about 10-15%.
  • polydiorganosiloxane (a) may also be referred to as a siloxane polymer and/or as a silicone polymer.
  • Polydiorganosiloxane (a) may be present in an amount of from 45 to 75% by weight of the composition, alternatively from 50 to 65% by weight of the composition.
  • the cross-linker (b) is one or more silanes or siloxanes which contain silicon bonded hydrolysable groups such as acyloxy groups (for example, acetoxy, octanoyloxy, and benzoyloxy groups); ketoximino groups (for example dimethyl ketoximo, and isobutylketoximino); alkoxy groups (for example methoxy, ethoxy, iso-butoxy and propoxy) and alkenyloxy groups (for example isopropenyloxy and 1-ethyl-2-methylvinyloxy).
  • acyloxy groups for example, acetoxy, octanoyloxy, and benzoyloxy groups
  • ketoximino groups for example dimethyl ketoximo, and isobutylketoximino
  • alkoxy groups for example methoxy, ethoxy, iso-butoxy and propoxy
  • alkenyloxy groups for example isopropenyloxy and 1-ethyl
  • the molecular structure can be straight chained, branched, or cyclic.
  • the cross-linker preferably has at least three or four hydroxyl and/or hydrolysable groups per molecule which are reactive with the hydroxyl and/or hydrolysable groups in organopolysiloxane (a).
  • the fourth group is suitably a non-hydrolysable silicon-bonded organic group.
  • These silicon-bonded organic groups are suitably hydrocarbyl groups which are optionally substituted by halogen such as fluorine and chlorine.
  • fourth groups include alkyl groups (for example methyl, ethyl, propyl, and butyl); cycloalkyl groups (for example cyclopentyl and cyclohexyl); alkenyl groups (for example vinyl and allyl); aryl groups (for example phenyl, and tolyl); aralkyl groups (for example 2-phenylethyl) and groups obtained by replacing all or part of the hydrogen in the preceding organic groups with halogen.
  • the fourth silicon-bonded organic group is methyl.
  • Silanes and siloxanes which can be used as cross-linkers include alkyltrialkoxysilanes such as methyltrimethoxysilane (MTM) and methyltriethoxysilane, alkenyltrialkoxy silanes such as vinyltrimethoxysilane and vinyltriethoxysilane, isobutyltrimethoxysilane (iBTM).
  • alkyltrialkoxysilanes such as methyltrimethoxysilane (MTM) and methyltriethoxysilane
  • alkenyltrialkoxy silanes such as vinyltrimethoxysilane and vinyltriethoxysilane
  • iBTM isobutyltrimethoxysilane
  • silanes include ethyltrimethoxysilane, vinyltriethoxysilane, phenyltrimethoxysilane, alkoxytrioximosilane, alkenyltrioximosilane, 3,3,3-trifluoropropyltrimethoxysilane, methyltriacetoxysilane, vinyltriacetoxysilane, ethyl triacetoxysilane, di-butoxy diacetoxysilane, phenyl-tripropionoxysilane, methyltris(methylethylketoximo)silane, vinyl-tris-methylethylketoximo)silane, methyltris(methylethylketoximino)silane, methyltris(isopropenoxy)silane, vinyltris(isopropenoxy)silane, ethylpolysilicate, n-propylorthosilicate, ethylorthosilicate, dimethylmethyl
  • cross-linker (b) may comprise a silyl functional molecule containing two or more silyl groups, each silyl group containing at least one —OH or hydrolysable group, the total of number of —OH groups and/or hydrolysable groups per cross-linker molecule being at least 3.
  • a disilyl functional molecule comprises two silicon atoms each having at least one hydrolysable group, where the silicon atoms are separated by an organic or siloxane spacer.
  • the silyl groups on the disilyl functional molecule may be terminal groups.
  • the spacer may be a polymeric chain having a siloxane or organic polymeric backbone. In the case of such siloxane or organic based cross-linkers the molecular structure can be straight chained, branched, cyclic or macromolecular.
  • the viscosity of the cross-linker will be within the range of from 0.5 mPa ⁇ s to 80,000 mPa ⁇ s at 25° C., alternatively 0.5 mPa ⁇ s to 25,000 mPa ⁇ s at 25° C., alternatively 0.5 mPa ⁇ s to 10,000 mPa ⁇ s at 25° C. measured using a Brookfield viscometer.
  • disilyl polymeric cross-linkers with a silicone polymer chain bearing alkoxy functional end groups include polydimethylsiloxanes having at least one trialkoxy terminal where the alkoxy group may be a methoxy or ethoxy group.
  • Examples might include hexamethoxydisiloxane, hexaethoxydisiloxane, hexa-n-propoxydisiloxane, hexa-n-butoxydisiloxane, octaethoxytrisiloxane, octa-n-butoxytrisiloxane and decaethoxy tetrasiloxane.
  • cross-linker (b) may be a disilyl functional polymer, that is, a polymer containing two silyl groups, each having at least one hydrolysable group such as described by the formula R 3 3-t Si(X) t —Rv—Si(X) f R 3 3-f where each R 3 may be the same or different and is selected from aliphatic alkyl groups, aliphatic alkenyl groups and aromatic groups, alternatively R 3 is an alkyl group having from 1 to 6 carbons; X may be individually selected as hereinbefore described above and t and f are independently an integer of 1, 2 or 3, alternatively 2 or 3.
  • Rv is an alkylene (divalent hydrocarbon radical), alternatively an alkylene group having from 1 to 10 carbon atoms, or further alternatively 1 to 6 carbon atoms or a combination of said divalent hydrocarbon radicals and divalent siloxane radicals.
  • disilyl polymeric cross-linkers with an organic polymer chain bearing alkoxy functional end groups examples include 1, 6-bis(trimethoxy silyl)hexane.
  • compositions suitably contain cross-linker in at least a stoichiometric amount as compared to organopolysiloxane (a) described above.
  • the filler component (c) comprises:
  • Fillers (c) (i) are effectively reinforcing fillers.
  • the calcium carbonate present is a precipitated or ground calcium carbonate which, in each case, preferably has a BET specific surface area of >100 m 2 /g.
  • Reinforcing silica as defined for the purpose of this disclosure, is preferably fumed hydrophobic silica.
  • Commercial examples are available, for example, from Evonik under the name of Aerosil® 972, Aerosil® 974 and Aerosil® 812. This list is not exhaustive. Increasing the amount of the reinforcing silica rapidly increases the thixotropic character and non-sag properties of the material. Industry Information-“Technical Bulletin Fine Particles 63” available form Evonik.com provides further examples and guidance on the use of silica.
  • the reinforcing filler(s) may for example be ground calcium carbonate and/or precipitated calcium carbonate having a BET specific surface area of >100 m 2 /g, and optionally fumed and/or precipitated silica, each of which has independently been treated by a treating agent such as, for example, stearic acid or a stearate.
  • the surface treatment of filler component (c) (i) may be performed, for example with a fatty acid or a fatty acid ester such as a stearate, or with organosilanes, organosiloxanes, or organosilazanes e.g.
  • hexaalkyl disilazane or short chain siloxane diols to render the filler(s) hydrophobic and therefore easier to handle and obtain a homogeneous mixture with the other ingredients of the composition.
  • surface modified fillers do not clump and can be homogeneously incorporated into the composition. This results in improved room temperature mechanical properties of the uncured compositions.
  • reinforcement an “active” or reinforcing filler to improve an elastomer's mechanical properties, such as modulus, tensile strength or elongation at break.
  • reinforcement an “active” or reinforcing filler to improve an elastomer's mechanical properties, such as modulus, tensile strength or elongation at break.
  • the use of reinforcing fillers improves both the strength and stiffness characteristics of a cross-linked elastomer.
  • a filled cross-linked elastomer has significantly higher stiffness than an unfilled cross-linked elastomer with the same degree of deformation.
  • a filled cross-linked elastomer also has a considerably higher strength and deformation to break than an unfilled analogue.
  • the filler component (c) also comprises one or more fibrous fillers (c)(ii) selected from mineral fibrous fibers, bulk fibrous fibers, refractory fibrous fibers, basalt fibrous fibers or mixtures thereof.
  • the fibrous fillers (c)(ii) may include fibers composed of one or more metal oxides e.g. alkali metal oxides, alkali-earths metal oxides, aluminium oxides and iron oxides and mixtures thereof.
  • Non-exhaustive examples for fibrous fillers are commercial products obtained from Morgan Ceramics, available under the trade name Enfil® SH or RockForce®/Roxul grades available from Lapinus.
  • the filler component may additionally include Non-reinforcing fillers including non-fibrous metal oxides e.g. alkali metal oxides, alkali-earths metal oxides, aluminium oxides and iron oxides and mixtures thereof.
  • Non-reinforcing silica can be both fumed and/or precipitated silica particles with a BET specific surface area of ⁇ 100 m 2 /g.
  • the silica is hydrophobically treated to facilitate the incorporation in the composition.
  • Examples of commercially available hydrophobically non-reinforcing treated silicas include Aerosil® R9200, Sipernat® D10, Sipernat® D13 and Sipernat® D17.
  • non-reinforcing fillers have a BET specific surface area of ⁇ 100 m 2 /g) and reinforcing fillers have a BET specific surface area of >100 m 2 /g).
  • additives (g) may include but are not restricted to rheological modifiers; adhesion promoters, pigments, heat stabilizers, flame retardants, UV stabilizers, chain extenders, and fungicides and/or biocides and the like.
  • Optional additives (g) may also include one or more adhesion promoters such as
  • the adhesion promoter when present the adhesion promoter may be distilled prior to use.
  • flame retardants examples include aluminium trihydrate, chlorinated paraffins, hexabromocyclododecane, triphenyl phosphate, dimethyl methylphosphonate, tris(2,3-dibromopropyl) phosphate (brominated tris), and mixtures or derivatives thereof.
  • pigments examples include titanium dioxide, chromium oxide, bismuth vanadium oxide, iron oxides and mixtures thereof.
  • heat stabilizers include metal compounds such as red iron oxide, yellow iron oxide, ferric hydroxide, cerium oxide, cerium hydroxide, lanthanum oxide, copper phthalocyanine.
  • the amount of heat stabilizer present in a composition may range from 0.01 to 1.0% weight of the total composition.
  • Biocides may additionally be utilized in the composition if required. It is intended that the term “biocides” includes bactericides, fungicides and algicides, and the like. Suitable examples of useful biocides, which may be utilized in compositions as described herein, include, for the sake of example:
  • Carbamates such as methyl-N-benzimidazol-2-ylcarbamate (carbendazim) and other suitable carbamates, 10,10′-oxybisphenoxarsine, 2-(4-thiazolyl)-benzimidazole, N-(fluorodichloromethylthio)phthalimide, diiodomethyl p-tolyl sulfone, if appropriate in combination with a UV stabilizer, such as 2,6-di(tert-butyl)-p-cresol, 3-iodo-2-propinyl butylcarbamate (IPBC), zinc 2-pyridinethiol 1-oxide, triazolyl compounds and isothiazolinones, such as 4,5-dichloro-2-(n-octyl)-4-isothiazolin-3-one (DCOIT), 2-(n-octyl)-4-isothiazolin-3-one (OIT) and n-butyl-1,2-benzis
  • biocides might include for example Zinc Pyridinethione, 1-(4-Chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-ylmethyl)pentan-3-ol and/or 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole.
  • the fungicide and/or biocide may suitably be present in an amount up to 0.3% by weight of the composition and may be present in an encapsulated form where required such as described in EP2106418.
  • compositions may be provided to the user in a one-part curable product, which can be applied onto a substrate directly or alternatively in a multi-part, typically two-part, combination requiring the multiple parts to be mixed together immediately before use.
  • the composition as hereinbefore described may comprise a two-part composition comprising a base part and a curing agent.
  • the two-part compositions comprise a first component (base) that contains silanol-terminated diorganopolysiloxane (a), filler (c), i.e.
  • the base component comprises: siloxane polymer (a) in an amount of 50 to 90% by weight of the base composition, alternatively from 50 to 80% by weight of the base composition, (with a view to being a present in an amount of from 50 to 75% by weight of the total composition as hereinbefore described) and reinforcing fillers (c).
  • Reinforcing fillers (c) are present in an amount of from from 10 to 50% by weight of the composition, alternatively from 20 to 50% by weight of the composition wherein there may be a cumulative maximum of calcium carbonate and/or silica or calcium carbonate and optionally silica ((c) (i)) of up to 25% by weight of the composition and the remainder of the reinforcing filler relied upon in the composition is of type (c) (ii) fibrous fillers. Indeed, as previously mentioned the filler (c) may be solely comprised of type (c) (ii) fibrous fillers. In one alternative there may be from about 5 to 15% by weight of calcium carbonate and/or silica i.e.
  • component (c) of the base component may solely contain of type (c) (ii) fibrous fillers.
  • the non-reinforcing fillers may be present in the base composition in an amount of from 0% to 20% by weight of the base composition,
  • the catalyst package may contain:
  • the components of each part are mixed together in amounts within the ranges given above and then the base component composition and the catalyst package composition are inter-mixed in a predetermined ratio e.g. from 15:1 to 1:1, alternatively from 14:1 to 5:1 alternatively from 14:1 to 7:1. If the intended mixing ratio of the base component:catalyst package is 15:1 or greater then no filler will be generally utilized in the catalyst package. However, if the intended mixing ratio of the base component:catalyst package is less than 15:1 an increasing amount filler will be utilized in the catalyst package up to the maximum of 50% weight of the catalyst package, if the intended ratio is 1:1.
  • the moisture curable compositions can be prepared by mixing the ingredients employing any suitable mixing equipment.
  • the base composition is prepared in the following way:
  • compositions as provided herein can be seen to provide a good balance between their mechanical properties and inherent “bulk” volume resistivity, i.e. the inherent resistance of a tested specimen regardless of its shape or size with the higher the surface resistivity and/or volume resistivity, the lower the leakage current and the less conductive the material.
  • the composition herein upon cure provides a silicone elastomer having a volume resistivity which is ⁇ 2 ⁇ 10 15 ⁇ cm; alternatively is ⁇ 5 ⁇ 10 15 ⁇ cm. Not only does the composition provide such a good volume resistivity but it also is suitable for use as an adhesive.
  • Polydiorganosiloxane polymers (a) of different average degrees of polymerisation (DP) were utilised as depicted in the following Tables. They were generally polydimethylsiloxanes having dimethylhydroxy terminal groups unless otherwise indicated.
  • the CaCO 3 (c) (i) used in the examples was surface treated with stearic acid.
  • the mean particle size was 60-70 microns and BET surface area was 18-20 m 2 /g as per manufacturer's data.
  • the fibrous fillers (c) (ii) used in the following examples are commercial products Enfil® SH, Rockforce® MS603-Roxul® 1000, Rockforce® MS615-Roxul® 1000 and CoatForce® CF50.
  • Enfil® SH was obtained from Morgan Ceramics, and the others were obtained from Lapinus Fibres BV.
  • the composition and some properties of the fibers used as provided by their technical data sheets are summarized in the tables 1a-1c below.
  • the fibers consisted of predominantly SiO 2 , transition metals oxides, oxides of the alkali and alkali-earths elements.
  • Non-reinforcing silica can be both fumed and precipitated.
  • the inventors find it beneficial to use silica with hydrophobized surface to facilitate the incorporation in the matrix. Examples include (non-exhaustive list) Aerosil® R9200, Sipernat® D10, Sipernat® D13 and Sipernat® D17, all from Evonik Industries.
  • adhesion promoter used in this example was a carbasilatrane derivative which was a condensation product of reactive silanes and was made following the description in paragraph [0047] of WO2007037552A2 (Adhesion promoter A) assigned to Dow Corning.
  • the tin based catalyst (d) was Dimethyl Tin Di Neodecanoate, DMTDN
  • compositions are henceforth illustrated by the following Examples, in which compositions are provided in weight % (wt. %), unless otherwise indicated.
  • Viscosities were measured using a Brookfield® cone plate viscometer (RV DIII) using cone plate CP-52 for viscosities of 40,000 mPa ⁇ s and below and cone plate CP-51 for materials having viscosities greater than 40,000 mPa ⁇ s adapting the speed according to the polymer viscosity.
  • RV DIII Brookfield® cone plate viscometer
  • the volume resistivity of a typical calcium carbonate filled two-part sealant formulation was used as a reference.
  • the compositions of the base and curing agent parts are depicted below.
  • the base part and curing agent part were mixed together in a ratio of 10:1 in a volume ratio of 10:1.
  • Sheets of 2 mm thickness were prepared in the following manner: The Base and the curing agent were mixed at the appropriate ratio and placed between two teflonized foils. The foils were then pressed against each other using a using a hydraulic press (Agila) operated at room temperature of 23° C.+/ ⁇ 1° C. Thus obtained protected sheets were left to cure in controlled conditions (25° C. and 50% relative humidity) for 3 weeks. Then the foils were removed and a square piece were cut out of the cure sheets for the volume resistivity measurement.
  • Agila hydraulic press operated at room temperature of 23° C.+/ ⁇ 1° C.
  • the volume resistivity is measure upon the application of 500 V current for 5 minutes.
  • the experiments were conducted at room temperature of 21-23° C. and relative humidity of 50+/ ⁇ 10%. The reported values are average of 3 independent measurements.
  • Volume resistivity was determined using a 16008B Resistivity Cell supplied by Keysight Technologies in combination with a 4339B High Resistance Meter, DC from the same supplier. According to the equipment supplier this equipment is suitable for accurately measuring volume resistance values up to 1.6 ⁇ 10 16 ⁇ cm.
  • the reference elastomeric material made from the two-part composition depicted in Tables 2a and 2b above gave a value of 1.3 ⁇ 10 15 which is less than 2.0 ⁇ 10 15 as required herein and therefore is not suitable for use in an electronic environment.
  • the base was prepared using a Hauschield mixer model DAC 400.1 FVZ, although alternatively planetary mixers could have been utilised.
  • Formulation curing agents CA1 CA2 (wt. %) (wt. %) aminoethylaminopropyl-3-methoxy-silane 2.0% 2.7% Trimethyl terminated polydimethylsiloxane 38.3% 51.0% having a viscosity of 12,500 mPa ⁇ s at 25° C.
  • Aerosil® R 974 used in the curing agent composition is a hydrophobic fumed silica post-treated with dimethyl-dichloro-silane from Evonik Industries. Specific surface area is 200 m 2 /g according to technical datasheet.
  • the curing agent was generally prepared using a Hauschield mixer model DAC 400.1 FVZ, although alternatively planetary mixers could have been utilised.
  • durable adhesion means that the adhesive, once cast on a substrate and cured is able to withstand three weeks weathering test without showing more than 50% adhesive failure in the last step (step 3 below). (method 1).
  • Method 2 the durability of adhesion can be assessed using adhesion durability test pieces (as described in method 2 here below).
  • This method provides also mechanical properties of the adhesive, which is an advantage.
  • Method 2 is time consuming as it stipulates 30 days of cure, whereas method 1 allows the discarding of bad (poorly performing) adhesive after one or two weeks of ageing.
  • Adhesive failure refers to the situation when the coating detaches cleanly (peels off) from the substrate.
  • Cohesive failure (CF) is observed when the coating itself breaks without detaching from the substrate (for example, steel plate).
  • CF Cohesive failure
  • a mixed failure mode may be observed; that is some areas peel-off (i.e. AF) while some remain covered with coating (i.e. CF).
  • % CF the portions of surface displaying CF
  • AF AF
  • a suitable material should withstand the entire sequence of 3 adhesion tests.
  • An adhesion durability test piece (also referred to as a “type H test piece”) was prepared by packing an admixture prepared by mixing separately stored base and curing agent compositions between two aluminum 4 ⁇ 5 cm plates.
  • the dimensions of the H-pieces were in accordance of EOTA-ETAG 002 (May 2012) document (p 32).
  • Om some instances Dow Chemical commercial OS1200 primer were applied prior to producing the H-pieces.
  • the H-pieces were allowed to cure for 30+/ ⁇ 4 days.
  • the adhesion durability test pieces were evaluated by measuring both tensile stress necessary to break the piece and elongation at break, following the methodology described in the EOTA-ETAG 002 (May 2012) document. In addition, the failure mode was evaluated by visual observation.
  • Accelerated ageing tests were performed in the following manner: H-pieces were cured for 7 days at RT and 50% RH. The cured H-pieces were then stored under water at 45° C. for seven days and then allowed to recover for 2 days before mechanical testing.
  • the inventive material combines volume resistivity of above 2.0 ⁇ 10 15 Ohm ⁇ cm and durable adhesion because the specimen showed 100% CF (e.g. above 90% CF) after 33 Days of cure and the specimens subject of accelerated ageing exhibit at least 90% CF (e.g. above 50% CF).
  • the specimen also passed Method 1 test criteria.

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GB201805382D0 (en) 2018-03-30 2018-05-16 Dow Silicones Corp Condensation curable compositions
US12448539B2 (en) 2019-12-17 2025-10-21 Dow Silicones Corporation Sealant composition
EP4077482A4 (fr) 2019-12-17 2023-08-16 Dow Silicones Corporation Préparation de polydiorganosiloxane
CA3162641C (fr) * 2019-12-23 2023-02-14 Maude DESROCHES Composition d'agent d'etancheite
CN112724925B (zh) * 2020-12-29 2022-08-02 广州市白云化工实业有限公司 双组份有机硅封装胶及其制备方法和应用
WO2023117440A1 (fr) * 2021-12-20 2023-06-29 Evonik Operations Gmbh Formulations adhésives comprenant des silanes et de la silice fumée hydrophobisée

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